含2,4-咪唑啉二酮的环十二酮衍生物的合成及杀菌活性  

Synthesis and Fungicidal Activity of Cyclododecanone Derivatives with Hydantoin

作　　者：陈守聪[1] 张春艳[1] 刘吉平[1] 王道全[1] 王明安[1] 

机构地区：[1]中国农业大学应用化学系,北京100193

出　　处：《有机化学》2010年第11期1768-1773,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20772150);"863"计划(No.2006AA10A209)资助项目

摘　　要：以环十二酮为原料合成α-取代环十二酮和α-取代环十二二酮,再与2,4-咪唑啉二酮膦酸酯和2-硫代-2,4-咪唑啉二酮分别发生Wittig-Horner反应和Knoevenagel缩合反应,合成了一系列目标化合物,它们的化学结构通过IR,1H NMR,13C NMR和元素分析进行了表征.初步生物活性测试结果表明,部分化合物10,11A,11B,12A,12B,13A,14B和16在50μg/mL浓度时对芦笋茎枯、茄绵疫以及油菜菌核病菌均有优良的抑制活性,抑制率在70%～98%之间,进一步的生物测试结果表明,化合物12B,13A和14B对芦笋茎枯的EC50值分别为15.80,31.34和44.26μg/mL.A series of novel cyclododecanone derivatives containing hydantoin/thiohydantoin were synthe-sized by the Wittig-Horner reaction and Knoevenagel condensation of α-substituted cyclododecanone and α-substituted 1,2-cyclododecandione prepared from cyclododecanone with hydantoin phosphate or thiohy-dantoin.Their structures were confirmed by IR,^1H NMR,^13C NMR spectra and elemental analysis.The pre-liminary bioassay showed that some of compounds such as 10,11A,11B,12A,12B,13A,14B and 16 exhibited good to excellent fungicidal activities with the range of 70%～98% inhibitory ratio against Phomopsis asparagi,Phytophthora parasitica and Sclerotinia sclerotiorum at the concentration of 50 mg/mL,the precise determination of EC50 data for 12B,13A and 14B were 15.80,31.34 and 44.26 mg/mL against P.asparagi,respectively.

关 键 词：α-取代环十二二酮 WITTIG-HORNER反应 KNOEVENAGEL缩合反应 杀菌活性 

分 类 号：O621.3[理学—有机化学]